So, how many women have you slept with?
Despite Salt’n’Peppa’s wise late-80s advice to get it all out and just talk about sex, baby, even more wise is to follow the sage advice in the following line: “Let’s talk about you and me.” Talking about yours and your significant other’s sex life together is healthy and wise. You both know where you stand, you know what you are fulfilling for your partner, and you know whether or not this is the girl who is going to be comfortable fulfilling your secret infantilism fantasies.
But where sex talk may not be healthy for your relationship is when it involves the past sex life of either partner. This question is one that could come up at any point in the relationship. It could spring from and it can be raised in many different contexts. The problem with the question is that is not easy to deflect. It’s the classic catch-22: if you talk, there is a good possibility that it will instill some sort of insecurity (or even worse, pity) in your partner; if you don’t talk, your partner will wonder what it is you are hiding. And whatever the truth is, your partner’s imagination will always be a thousand times worse than reality (hopefully).
Either way, when the issue comes up, you are going to have to say something or else this is going to hang over your relationship (and your sex life) until it is resolved. And like the big pink elephant in the room, it will grow and grow until no answer seems right.
One thing you need to know before answering this question is from whence it arose. Is she asking because you are so adept in the sack that only vast amounts of exotic experience could explain it? If this is the case, then consider it a tentative compliment. One that could turn on you if you start regaling her with tales of your sexual education. Whatever your experience, you will receive hearty applause if you play down your sexual experience (which may or may not impress her) and play up the fact that you pride yourself on placing a lot of emphasis on finding out what makes the woman you’re with feel good. If you really want to lay it on thick, tell her that you feel that women often get a raw deal in the sack and you feel it is your responsibility to make certain that she is pleasured.
Another possibility is that she has heard certain things about you and just wants to check out if you are going to be honest with her. Tread this one carefully. If you suspect that this is the context, ask her where this came from. If she expects you to be honest with her, then she has to be honest with you. Once you have the source, you will know where you stand in this possibly mine-filled discussion. Tell her that while you don’t think your past is important because she is the person who you want to be with, and are with exclusively, you will tell her if she can tell you why she thinks it is important. Another good question to ask is how she thinks this will better your relationship now. There is no sense in you being to only one in the hot seat.
Once she has answered these questions to your satisfaction, then assure her that nothing that has happened in your past has any bearing on your sex life with her. If you can, do your best to reassure her that yours is the best sex you have ever had, even if this is a lie. Nobody wins when one partner suddenly starts suffering from sexual insecurity.
If yours is a particularly colourful sexual past, then feel free to be selective about the details. It is your life and you shouldn’t be guilted into having regrets that your don’t need to have. You can divulge however much or little you feel comfortable sharing. Try to stick to her specific questions. If you slept with a certain person and she asks you about it, don’t lie. She wouldn’t be asking if she didn’t already know. Even if she finds this person distasteful, your past is yours, and it has no reflection on your current relationship. If you have regrets, feel free to share them. If she starts to get angry, remind her that she is the one who instigated this conversation despite your better judgment.
A final possibility is that your partner is very insecure, and feels like she isn’t measuring up to your past, or how she perceives your past as being. If this is the case, then you are in a bit of a bind because the more you avoid the discussion, the more convinced she will be that she is disappointing you and you just don’t want to tell her. The problem with insecure people is that they are slightly masochistic. She doesn’t really want to know, but her insecurities are forcing her to prove every doubt she has about herself. The best approach to start with is to just divert the conversation with compliments of the “I have never been with anyone as amazing as you, I’ll tell you that much” persuasion. Try to silence her questioning lips with kisses. This is your moment to shamelessly flex any romantic bone you have in your body. What she really wants is to feel secure, not to know. If you can do that without acting as though you are hiding something, rather the simply finding the topic boring because it doesn’t involve her, you could be a winner.
While honesty is underrated in relationships, there are certain details no girl wants or needs to know. If you have ever slept with a stripper or anyone in the adult entertainment industry, please don’t tell her. You’ll come off looking like a schlep and any body issues she has may come screaming to the forefront. Threesomes are also not good relationship talk, because she’ll instantly assume that you want her to have one. Also, tread carefully with any bi- or homosexual experiences you have had that she doesn’t know about. While sexual experimentation is healthy, many women are not ready to hear this, because no matter what, they simply cannot compete with that.